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Highly stereoselective hydrocarbation of terminal alkynes via Pt-catalyzed hydrosilylation/Pd-catalyzed cross-coupling reactions.

Organic letters (2001-03-30)
S E Denmark, Z Wang
ABSTRACT

[reaction: see text]. The formal addition of an aryl-H or alkenyl-H bond across a terminal alkyne has been accomplished by the combination of platinum-catalyzed hydrosilylation followed by palladium-catalyzed cross-coupling. The use of the t-Bu3P-Pt(DVDS) catalyst in combination with tetramethyldisiloxane gave excellent regio- and stereoselectivity with a number of alkyne substrates. Subsequent, fluoride-promoted cross-coupling proceeded in high yield and stereospecificity for a variety of aryl halides.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex solution, in xylene, Pt ~2 %

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